I wore dresses before I knew what transgenger was and I thought it was just a weird fetish / or phase. I actually forced myself to stop it, threw out my dresses, my bustiers, my shoes, my makeup, and my wigs because I thought it was wrong and sinful and indulging made me a bad person.
I did not wear dresses because I liked it (although I did like it). I wore dresses because it made me feel like a woman and that is what I really wanted.
What is the point? Society sucks and is absolutely monstrous to anyone who doesn't play into the subtle and shifting narrative it supports.
Someone who is a cis woman should, right now and not in hypothetical land, be able to shut down anyone who says shit about her wearing a dress with, "I am a woman." That will work, right now, just about anywhere in the United States. A trans woman trying the same should be granted the same privilege but she isn't.
Letting men wear dresses won't fix anything for trans women when the problem is having society at large recognize them as women in the first place. Trans women are absolutely seen as "just" men in dresses by a lot if people. Enough people that "man in a dress" is practically a trope for trans women right up there us with "tricking" unsuspecting men into having gay sex with us.